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Organizations have difficulty learning from rare and unusual events because of their inability to interpret these events. Because organizations develop habitual ways of interpreting events—often top down—they can easily miss the novelty of rare and unusual events, which prevents them from experiencing events “richly.” We propose a multilevel, multistaged model of organizational interpretation that highlights the important, but generally unacknowledged, role middle managers can play in helping organizations experience rare and unusual events richly. Our model accounts for the effect of cognitive biases and hierarchical context on organizational interpretation. Because of their proximity to the interpretations of both strategic and front-line managers, middle managers can encourage divergence in interpretations of managers across hierarchical levels during early stages of the interpretation process and can blend and synthesize the divergent interpretations of managers during later stages. In this way middle managers contribute to a dynamic process of organizational interpretation in which multiple filters from throughout the organization help frame and enrich interpretations of rare and unusual events, which enables organizational learning.